[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[N:10][C:11]([C:14]3[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=3)[C:17](OC)=[O:18])=[N:12][CH:13]=2)[CH2:4][CH2:3]1.[H-].C([Al+]CC(C)C)C(C)C.S([O-])([O-])(=O)=O.[Na+].[Na+].ClCCl>C1COCC1>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[N:12][C:11]([C:14]3[CH:15]=[C:16]([CH2:17][OH:18])[CH:21]=[CH:22][CH:23]=3)=[N:10][CH:9]=2)[CH2:6][CH2:7]1
860 mg (2.75 mmol) of methyl 3-[5-(4-methylpiperazin-1-yl)pyrimidin-2-yl]-benzoate are dissolved in 16 ml of THF, and 13.8 ml (13.8 mmol) of 1 M diisobutylaluminium hydride in THF are added dropwise at room temperature, and the reaction mixture is stirred at room temperature for 1 h. A further 13.8 ml (13.8 mmol) of 1 M diisobutylaluminium hydride in THF are added dropwise, and the reaction mixture is stirred at room temperature for 1 h. 3 ml of saturated sodium sulfate solution are added to the reaction mixture with ice cooling. Dichloromethane is added to the gelatinous mixture, which is then stirred for 30 min and filtered. The filtrate is dried over sodium sulfate and evaporated. Yield: 300 mg, yellow solid. The product is reacted further without further purification; HPLC: 1.68 min (method B); ESI: 285 (M+H).
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